Dye.



DYE. I s I V l Y 1,014,204, Specification of Letters Patent. Patented Jan, 9,1912, No Drawing. I Application filed December 7, 1910. Serial No. 596,125. 7

- i l I Q To all whom it may contem: The new dyes are after being dried and Be it known that I, WILHnLM BERGHEL- pulverized in the shape of their alkaline MANN, doctor of philosophy, chemist, citisalts dark powders" whi h are solublein r Zen of the German Empire, residing at water generally with from a red to blue Vohwinkel, near Elberfeld, Germany, haye color and which are soluble in concentrated invented new and useful Improvements in sulfuric ac1d generally with from a red to New Dye, of which the followingis a speciviolet-red I color. They dye wool generally fication. from red to blue to violet shades.

My invention relates to the manufacture In order to illustrate the new process and production of new compounds of the more fully the following example is given, anthracene series. The process for their the parts-being by weight A mixture of production consists in treating alpha-amino- 25 parts of 1. l-diaminoanthraquinone, 50 anthraquinones with alkylene oxids, espeparts v of glacial acetic acid, '50 \parts of cially ethylene oxid: ethylene oxid and 250 parts of nitrobenzene L is heated for several days to 3 035 C. until I it has assumed a blue coloration. p cm The new product thus obtained is. filtered glycid: off and dried, and has probably the follow-1 ou-cIn-oH ing constitution:

J o'm-onzon 2 I propylene 02nd: I

on CH a 0. -co' l These new compounds contain in' their too molecule the characteristic group Xg on I IIIHC3H3\-R om-cmon I I 10 parts of it are then introduced into 100 in which R stands for a substituting group, Parts of fu'mmg s111fur1 c ac 1d P cent- A for the anthraquinone nucleus. 3) fi the m P Stlrred at 9 If instead of monoaminoanthraquinones untll a sample 15 comRletely soluble m diaminoanthraquinones are employed in the W It 15 then R -e mto 600 .P O process, the free valency in the above group we Water, the y 1S t -1 out 71th i l d b th group mon salt and drled. It.1s a dark powder OH which is soluble in water with pure blue NH-C2H color and which is soluble in concentrated R 4 sulfuric .acid with a violet-red color. It so that diaminoanthraquinone derivatives y W001 p blue shades a llgh nd contain in their molecule the characteristic 'pr ly the followmg constltutloni group 1 CHzCHa0--SO3H V N g 1\IH 1 \R V I- IHCzHa I (W R I By treating the new compounds thus produced with sulfonating agents soluble new it v dyestufis are obtained. ,It is not necessary l to lntroduce sulfonic groups into the prod UNITED STATES PATENT OFF-10 WILHELIMZ IBERCHELMANN,

TO FARBENFAIBRIKEN VORM. -FRIEDR. A. CORPORATION OF GERMANY.

ucts obtained by the action of alkylene' 'oxlds if the starting materials contain al- IBAYER 80 (30., OF

The process is carried out in an analogous manner as described in the example on ready sulfonic. groups.

or vonwINKEn, NEAR ELBERFELD, GER ANY,- AssIsnoR. ELBEREELD, GERMANY,

starting from other alpha-aminoanthraqui nones, e. g." 1.5-diaminoanthraquinone, 1-

amino-anthraquinone, 1.4 amino oxy 1 anthr aquinone, para-'diamino-anthrarufine disulfonic acid, etc.

j Other sulfonating agents, e. g. chlorosulfonic acid,.etc., may be used.-

I claim 1. The herein described new dyestuffs obtainable from l-aminoanthraquinones and alkylene oxids containing in their molecule the characteristic group in which R stands for a substituting group and A for the anthraquinone nucleus which are after being dried and pulverized in the shape of their alkaline salts dark powders soluble in water generally with from a red to blue color, soluble in concentrated sulfuric acid generally withlfrom a red to violet-red .color;' and dyeing Wool generally from red to blue to violet shades, substan-' tially as described.

2. The herein described new dyestufi ob-' tainable from lA-diaminoanthraquinone and ethylene oxid, having probably the following constitution:

CHr-CHgO-SOaH CHz-CHzO-SOgI-I which dye is after being dried and pulverized in the shape of its sodium salt a dark powder soluble in water with a pure blue color and soluble in concentrated sulfuric acid with a violet-red color; dyeing wool .pure blue shades fast to light, substantially as described.

-In testimony whereof I have hereunto set my hand .in the presence of two subscribing Witnesses.

WILHELM BERGHELMANN. [L. 8.] Witnesses CHAS. J. WRIGHT, ALFRED HENKEL. 

